phenyl 3,4-di-O-acetyl-2-chlorodifluoromethyl-2-deoxy-1-thio-α-D-arabinopyranoside

Base Information

• Chemical Name: phenyl 3,4-di-O-acetyl-2-chlorodifluoromethyl-2-deoxy-1-thio-α-D-arabinopyranoside
• CAS No.: 581099-61-8
• Molecular Formula: C₁₆H₁₇ClF₂O₅S
• Molecular Weight: 394.824
• Mol file: 581099-61-8.mol

Synonyms:phenyl 3,4-di-O-acetyl-2-chlorodifluoromethyl-2-deoxy-1-thio-α-D-arabinopyranoside

Chemical Property of phenyl 3,4-di-O-acetyl-2-chlorodifluoromethyl-2-deoxy-1-thio-α-D-arabinopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3,4-di-O-acetyl-2-chlorodifluoromethyl-2-deoxy-1-thio-α-D-arabinopyranoside

There total 3 articles about phenyl 3,4-di-O-acetyl-2-chlorodifluoromethyl-2-deoxy-1-thio-α-D-arabinopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 49.0%

thiophenol (108-98-5) + 1,3,4-tri-O-acetyl-2-chlorodifluoromethyl-2-deoxy-β-D-arabinopyranoside (581099-47-0) → phenyl 3,4-di-O-acetyl-2-chlorodifluoromethyl-2-deoxy-1-thio-α-D-arabinopyranoside (581099-61-8) + phenyl 3,4-di-O-acetyl-2-chlorodifluoromethyl-2-deoxy-1-thio-β-D-arabinopyranoside (581099-60-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃;

DOI:10.1055/s-2003-38076

Reference yield:

3,4-di-O-acetyl-D-arabinal (3152-43-0,3945-17-3,3945-18-4,86257-92-3,89921-34-6,89921-35-7,101052-70-4) → phenyl 3,4-di-O-acetyl-2-chlorodifluoromethyl-2-deoxy-1-thio-α-D-arabinopyranoside (581099-61-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / aq. NaHCO₃; Na₂S₂O₄ / acetonitrile / 4 h / 10 °C

2: 84 percent / pyridine / 20 °C

3: 45 percent / BF₃*Et₂O / CH₂Cl₂ / 20 °C

With pyridine; sodium dithionite; boron trifluoride diethyl etherate; sodium hydrogencarbonate; In dichloromethane; acetonitrile;

DOI:10.1055/s-2003-38076

Reference yield:

3,4-di-O-acetyl-2-chlorodifluoromethyl-2-deoxy-D-arabinopyranose → phenyl 3,4-di-O-acetyl-2-chlorodifluoromethyl-2-deoxy-1-thio-α-D-arabinopyranoside (581099-61-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / pyridine / 20 °C

2: 45 percent / BF₃*Et₂O / CH₂Cl₂ / 20 °C

With pyridine; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1055/s-2003-38076

upstream raw materials:

thiophenol

1,3,4-tri-O-acetyl-2-chlorodifluoromethyl-2-deoxy-β-D-arabinopyranoside

3,4-di-O-acetyl-D-arabinal

Downstream raw materials:

phenyl 2-chlorodifluoromethyl-2-deoxy-1-thio-α-D-arabinopyranoside